On Wednesday night, Paul Skenes was unanimously honored with the NL Cy Young award, making waves not only for his exceptional talent but also for the team he represents—the Pittsburgh Pirates. A team that hasn’t seen playoff action since 2015 or a series victory since 1979, the Pirates now find themselves in a narrative that speculates about Skenes’ future, hinting at a potential departure.

Inevitably, the New York Yankees have emerged as a possible future destination for Skenes. The buzz surrounding this idea gained traction during the second day of the General Managers’ meetings in Las Vegas. This was spurred by an NJ.com article in which a Pittsburgh teammate revealed Skenes’ apparent aspirations to don the Yankees’ iconic pinstripes someday.

Skenes’ only encounter with the Yankees thus far occurred during a brief yet impressive two-inning performance at Yankee Stadium on the final Saturday of the 2024 season. During this cameo, he struck out prominent players Juan Soto and Aaron Judge. Adding to the spectacle was the presence of his gymnast girlfriend, Livvy Dunne, who cheered him on from the stands.

At the time of this performance, Skenes was wrapping up his rookie season, during which he outshone Jackson Merrill to claim the Rookie of the Year title. His contributions were notable on a 76-win team, and while little was mentioned about his future prospects with the Yankees then, such discussions are now surfacing. These talks will likely persist unless the Pirates secure Skenes with a long-term contract or decide to trade him.

This scenario isn’t quite as dramatic as Gerrit Cole’s childhood moment at the 2001 World Series, where he famously held a sign professing his Yankee fandom. However, the chatter has become prevalent enough that Pirates GM Ben Cherrington has felt compelled to address the speculation.

That was at the end of his rookie season when he beat Jackson Merrill for Rookie of the Year while joining a 76-win team so there was no speculation then but it figures to be the kind of thing to appear now and occasionally in the future until the Pirates lock him up to a long-term deal or actually trade him.

It is not quite like Gerrit Cole going to the World Series in 2001 as a child with a sign proclaiming his massive Yankee fandom but it is out there so much to the point that GM Ben Cherrington even addressed the topic.

“What we’re going to focus on is just how do we win games with him in a Pirates uniform,” Cherrington told reporters. “I have a ton of respect for the Yankees but we’ll just focus on what we need to do.”

And what Cherrington and the Pirates need to do is spend enough to build a team around Skenes. Skenes won his Cy Young Award with 10 wins. It is tied for the fewest total for a starter to win the award in a full season.

Skenes joined Jacob deGrom as the only pitchers with 10 wins to win the award in a full season.

DeGrom was 10-9 with a 1.70 ERA and 269 strikeouts while pitching for a 77-win version of the Mets in 2018, whose payroll back then was roughly $150 million.

Skenes was 10-10 with a 1.97 ERA and 216 strikeouts while pitching about 30 fewer innings than deGrom. In all 10 of his losses, the Pirates scored three runs or fewer, including four times when they were shutout. In 19 of his 32 starts, the Pirates scored three runs or fewer.

The lack of run support resulted in the Pirates going 17-15 in games he started as part of a 71-91 finish for Pittsburgh, which lost at least 90 games for the 14th time since 1992.

If those things sound familiar it is because they are similar if not worse. The Mets were 14-18 in deGrom’s starts in 2018 and it was because of the run support issue.

Those Mets scored three runs or fewer in 20 of deGrom’s 32 starts in 2018, including in seven of his nine losses.

The difference between Skenes and deGrom was payroll disparities. The Pirates played with a roughly $87 million payroll, a figure that is the same as their final number of 2024 along with two million less than the final figure of 2019, which would have been Cole’s free agent year with them if he was not dealt to the Houston Astros following the 2017 season.

The Skenes out of Pittsburgh talk and links to the Yankees will persist until proven otherwise. The Pirates are consistently in the bottom of payrolls, finishing in the bottom-five 16 times since 2007 when Bob Nutting bought the team.

“In a nice way, it’s really simple because what matters most to (Skenes) is what matters to us,” Cherington told reporters. “Win more games. That’s the focus because that’s what is going to be most important to him. What probably gives us the best chance to keep him in Pittsburgh for longer is winning games, and that’s what we need to do anyway.

“So in a way it helps simplify it and focus it. My conversations with him, the only thing we talk about is winning and how to do that.”

For now, the Pirates may raise payroll by an incremental amount, but it is unknown if it will be good enough to get them into contention in a league where 83 wins led to a playoff berth for the Cincinnati Reds.

Until anyone starts to see Pittsburgh produce a payroll in the middle of the pack, the buzz of when Skenes leaves will overshadow things, though it is hard to believe his departure is coming within the next year.